JPS625928B2 - - Google Patents
Info
- Publication number
- JPS625928B2 JPS625928B2 JP53016457A JP1645778A JPS625928B2 JP S625928 B2 JPS625928 B2 JP S625928B2 JP 53016457 A JP53016457 A JP 53016457A JP 1645778 A JP1645778 A JP 1645778A JP S625928 B2 JPS625928 B2 JP S625928B2
- Authority
- JP
- Japan
- Prior art keywords
- vinylquinoline
- vinylpyridine
- exchange resin
- anion exchange
- copolymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000178 monomer Substances 0.000 claims description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003957 anion exchange resin Substances 0.000 claims description 8
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 7
- XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical compound C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- DZGGGLJOCYPKHN-UHFFFAOYSA-N 4-ethenylquinoline Chemical compound C1=CC=C2C(C=C)=CC=NC2=C1 DZGGGLJOCYPKHN-UHFFFAOYSA-N 0.000 description 1
- LBFCGFOMLOEOBR-UHFFFAOYSA-N 6-ethenylquinoline Chemical compound N1=CC=CC2=CC(C=C)=CC=C21 LBFCGFOMLOEOBR-UHFFFAOYSA-N 0.000 description 1
- HITKJZPTWAZTDK-UHFFFAOYSA-N 7-ethenylquinoline Chemical compound C1=CC=NC2=CC(C=C)=CC=C21 HITKJZPTWAZTDK-UHFFFAOYSA-N 0.000 description 1
- WRTNGGDLQMFSJL-UHFFFAOYSA-N 8-ethenylquinoline Chemical compound C1=CN=C2C(C=C)=CC=CC2=C1 WRTNGGDLQMFSJL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【発明の詳細な説明】
本発明は産業上有用なる新規な陰イオン交換樹
脂の製造方法に係り、更に詳しくは、ビニルピリ
ジン、ビニルキノリンおよび架橋性ジビニル単量
体を触媒の存在下重合することを特徴とする弱塩
基性陰イオン交換樹脂の製造方法に関する。
ビニルピリジンを架橋性ジビニル単量体、例え
ばジビニルベンゼンにて架橋せる共重合体は弱塩
基性陰イオン交換樹脂として知られている。これ
らは生化学、医薬等の分野において使用されてい
るが、活性力において劣り、その向上が望まれて
いる。本発明はビニルピリジン、ビニルキノリン
および架橋性ジビニル単量体を触媒の存在下にお
いて重合することを特徴とする陰イオン交換樹脂
に係る。以下本発明について説明する。
本発明に使用されるビニルピリジンは２―ビニ
ルピリジン、４―ビニルピリジン等が挙げられ
る。
次にビニルキノリンについて述べれば、２―ビ
ニルキノリン、４―ビニルキノリン、６―ビニル
キノリン、７―ビニルキノリン、８―ビニルキノ
リン等が挙げられる。これらの単量体の混合比率
は任意に行ないうる。これらの単量体を架橋する
ために用いる架橋性ジビニル単量体はジビニルベ
ンゼン、ジビニルトルエン、ジビニルナフタレン
等の芳香族単量体、ジアクリル酸エチレングリコ
ールエステル、ジメタクリル酸エチレングリコー
ルエステル等の脂肪族単量体が挙げられ、所望の
共重合体の性質により変えられる。
それらを重合する方法としては、懸濁重合、乳
化重合等が好適である。重合を開始するにあたつ
て触媒が用いられる。かかる触媒は、このような
ビニル単量体の重合反応に用いられるもののなか
から適宜選べばよく、過酸化ベンゾイル、ｔ―ブ
チルパ―オキサイド、過酸化ラウロイル、アゾイ
ソブチロニトリル等が用いられる。これらは単量
体混合物に対し0.1〜５％程度が好適である。そ
の重合温度は、通常ラジカル開始剤の分解温度以
上であればよく、例えば常圧下では50〜100℃の
範囲で行なわれる。また重合の際に、重合系中に
生成共重合体を膨潤し、水に難溶性又は不溶性の
有機溶媒、生成共重合体を膨潤せず、水に難溶性
又は不溶性の有機溶媒（所謂沈澱剤）又は線状重
合体を添加しても同様に弱塩基性陰イオン交換樹
脂が得られる。
次に実施例により本発明を説明する。
実施例
４―ビニルピリジン51ｇ、２―ビニルキノリン
17.2ｇ、工業用ジビニルベンゼン9.3ｇ（純度58.2
％：残りは主としてエチルビニルベンゼンより成
る）及び過酸化ベンゾイル１ｇからなる均一混合
物を予め分散剤、ゼラチン、食塩、水酸化ナトリ
ウム等を水316ｇに溶解した分散水溶液中に装入
する。これを撹拌し、約70〜80℃で８時間重合し
た。
生成した共重合体粒子を濾過し、水洗し、乾燥
し、白色の共重合体70ｇを得た。第１図に赤外線
吸収スペクトルを示す。
この生成物をよく水和後、常法により弱塩基性
交換容量を測定した結果2.2meq／ｇであつた。
また上記処方中に沈澱剤を添加し重合しても、
同様の弱塩基性陰イオン交換樹脂が得られた。
参考例
４―ビニルピリジン及びジビニルベンゼンを使
用し、実施例と同様の方法で懸濁重合を行ない、
共重合体粒子（ジビニルベンゼン含量６％）を比
較例とした。
この共重合体粒子の弱塩基性交換容量は
2.1meq／ｇであつた。
実施例及びこの４―ビニルピリジン―ジビニル
ベンゼン共重合体粒子を使用し、アミノ酸の吸着
試験を行なつた。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel anion exchange resin that is industrially useful, and more specifically, it involves polymerizing vinylpyridine, vinylquinoline, and a crosslinkable divinyl monomer in the presence of a catalyst. The present invention relates to a method for producing a weakly basic anion exchange resin. A copolymer in which vinylpyridine is crosslinked with a crosslinkable divinyl monomer, such as divinylbenzene, is known as a weakly basic anion exchange resin. Although these are used in fields such as biochemistry and medicine, they are inferior in activity and it is desired to improve their activity. The present invention relates to an anion exchange resin characterized in that vinylpyridine, vinylquinoline, and a crosslinkable divinyl monomer are polymerized in the presence of a catalyst. The present invention will be explained below. Examples of the vinylpyridine used in the present invention include 2-vinylpyridine and 4-vinylpyridine. Next, referring to vinylquinoline, examples include 2-vinylquinoline, 4-vinylquinoline, 6-vinylquinoline, 7-vinylquinoline, 8-vinylquinoline, and the like. The mixing ratio of these monomers can be adjusted arbitrarily. The crosslinkable divinyl monomers used to crosslink these monomers include aromatic monomers such as divinylbenzene, divinyltoluene, and divinylnaphthalene, and aliphatic monomers such as ethylene glycol diacrylate and ethylene glycol dimethacrylate. Monomers may be mentioned and may vary depending on the properties of the desired copolymer. Suitable methods for polymerizing them include suspension polymerization and emulsion polymerization. A catalyst is used to initiate the polymerization. Such a catalyst may be appropriately selected from those used in the polymerization reaction of vinyl monomers, and examples include benzoyl peroxide, t-butyl peroxide, lauroyl peroxide, azoisobutyronitrile, and the like. A suitable amount of these is about 0.1 to 5% based on the monomer mixture. The polymerization temperature may be generally higher than the decomposition temperature of the radical initiator, and is carried out, for example, in the range of 50 to 100°C under normal pressure. In addition, during polymerization, organic solvents that swell the copolymer produced in the polymerization system and are sparingly soluble or insoluble in water, organic solvents that do not swell the copolymer and are sparingly soluble or insoluble in water (so-called precipitating agents). ) or a linear polymer can similarly yield a weakly basic anion exchange resin. Next, the present invention will be explained with reference to examples. Example 4-vinylpyridine 51g, 2-vinylquinoline
17.2g, industrial divinylbenzene 9.3g (purity 58.2
%: the remainder mainly consists of ethylvinylbenzene) and 1 g of benzoyl peroxide is charged into an aqueous dispersion solution in which a dispersant, gelatin, salt, sodium hydroxide, etc. are previously dissolved in 316 g of water. This was stirred and polymerized at about 70-80°C for 8 hours. The produced copolymer particles were filtered, washed with water, and dried to obtain 70 g of a white copolymer. Figure 1 shows the infrared absorption spectrum. After thoroughly hydrating this product, the weak base exchange capacity was measured by a conventional method and was found to be 2.2 meq/g. Also, even if a precipitant is added to the above formulation and polymerized,
A similar weakly basic anion exchange resin was obtained. Reference Example 4-Using vinylpyridine and divinylbenzene, suspension polymerization was carried out in the same manner as in the example,
Copolymer particles (divinylbenzene content: 6%) were used as a comparative example. The weak basic exchange capacity of this copolymer particle is
It was 2.1meq/g. Using the examples and the 4-vinylpyridine-divinylbenzene copolymer particles, an amino acid adsorption test was conducted. 【table】
実施例で製造した弱塩基性陰イオン交換樹脂の
赤外線吸収スペクトルを示す。
1 shows an infrared absorption spectrum of a weakly basic anion exchange resin produced in an example.
Claims (1)
性ジビニル単量体を触媒の存在下重合することを
特徴とする弱塩基性陰イオン交換樹脂の製造方
法。1. A method for producing a weakly basic anion exchange resin, which comprises polymerizing vinylpyridine, vinylquinoline, and a crosslinkable divinyl monomer in the presence of a catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1645778A JPS54110186A (en) | 1978-02-17 | 1978-02-17 | Method of mamufacturing weak basic anion exchange resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1645778A JPS54110186A (en) | 1978-02-17 | 1978-02-17 | Method of mamufacturing weak basic anion exchange resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54110186A JPS54110186A (en) | 1979-08-29 |
| JPS625928B2 true JPS625928B2 (en) | 1987-02-07 |
Family
ID=11916772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1645778A Granted JPS54110186A (en) | 1978-02-17 | 1978-02-17 | Method of mamufacturing weak basic anion exchange resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54110186A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63130605A (en) * | 1986-11-20 | 1988-06-02 | Tokuyama Soda Co Ltd | Method for producing anion exchanger |
| CA2136324A1 (en) * | 1992-07-08 | 1994-01-20 | Steven Joseph Brickner | 5'-indolinyl oxazolidinones useful against mycobacterium tuberculosis |
| KR101866265B1 (en) * | 2009-07-28 | 2018-06-11 | 인스트랙션 게엠베하 | Specific sorbent for binding proteins and peptides, and separation method using the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51144394A (en) * | 1975-06-09 | 1976-12-11 | Asahi Chem Ind Co Ltd | Process for producing porous anion exchange resin |
| JPS51144393A (en) * | 1975-06-09 | 1976-12-11 | Asahi Chem Ind Co Ltd | Process for producing porous anion exchange resin |
| JPS52140592A (en) * | 1976-05-18 | 1977-11-24 | Sumitomo Chem Co Ltd | Preparation of porous resins having nitrogen-containing heterocyclic structure |
| JPS5310680A (en) * | 1976-07-16 | 1978-01-31 | Sumitomo Chem Co Ltd | Preparation of hig-molecular weight compound comprising vinyl pyridine |
-
1978
- 1978-02-17 JP JP1645778A patent/JPS54110186A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51144394A (en) * | 1975-06-09 | 1976-12-11 | Asahi Chem Ind Co Ltd | Process for producing porous anion exchange resin |
| JPS51144393A (en) * | 1975-06-09 | 1976-12-11 | Asahi Chem Ind Co Ltd | Process for producing porous anion exchange resin |
| JPS52140592A (en) * | 1976-05-18 | 1977-11-24 | Sumitomo Chem Co Ltd | Preparation of porous resins having nitrogen-containing heterocyclic structure |
| JPS5310680A (en) * | 1976-07-16 | 1978-01-31 | Sumitomo Chem Co Ltd | Preparation of hig-molecular weight compound comprising vinyl pyridine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54110186A (en) | 1979-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5244926A (en) | Preparation of ion exchange and adsorbent copolymers | |
| US3637535A (en) | Anion exchanger with sponge structure | |
| DE3380847D1 (en) | The manufacture of crosslinked copolymer beads, the copolymer beads themselves and their use as adsorbents or, on incorporation or addition of functional groups, as ion exchange resins | |
| US3586646A (en) | Cation exchanger with sponge structure | |
| US3941724A (en) | Production of amphoteric resins in a reaction medium comprising formic acid | |
| US3907720A (en) | Insoluble porous polymeric iodine complexes useful as bactericides | |
| JPH0524922B2 (en) | ||
| JPS5833018B2 (en) | Shinsuiseiji Yugotai Matrix Oyuusuru Ryousei Ion Kokantaino Seizouhouhou | |
| US4139499A (en) | Thermally reversible amphoteric ion exchange resins of improved demineralization capacity | |
| US3367889A (en) | Process for the preparation of macroreticular-structured copolymers | |
| US6525156B1 (en) | Styrene-containing popcorn polymers, method for producing same and utilisation | |
| US4238569A (en) | Preparation of hydrophilic material for gel chromatography | |
| JPS6250486B2 (en) | ||
| JPS6151007A (en) | Production of crosslinked polyvinylamine | |
| JPS625928B2 (en) | ||
| JP4146536B2 (en) | Process for the preparation of low-bleeding cation exchangers | |
| US4184020A (en) | Preparation of hydrophilic material for gel chromatography | |
| US4130512A (en) | Ion exchange materials | |
| EP0045824A1 (en) | Ion exchange material, its preparation and use | |
| US2768991A (en) | Preparation of cation exchangers from co-polymerized carboxylic acid and cross-linking agent | |
| JP2007505209A (en) | Improved solventless sulfonation of exchange resins | |
| US4342839A (en) | Method of manufacture of ion exchange resins | |
| JP2000007711A (en) | Preparation of crosslinked spherical polymer | |
| JPH07330818A (en) | Production of spherical cross-linked copolymer | |
| USRE26934E (en) | Chromatographic separation of substances of different molec- ular weight |